


The First Night With The Baron

by DiaryOfMilo



Series: The Baron's House [1]
Category: Original Work
Genre: Anal Fingering, Anal Sex, Brothels, Creampie, Fantasy, Feminization, First Time, Loss of Virginity, M/M, Magic, Male Protagonist, Science Fiction & Fantasy
Language: English
Status: Completed
Published: 2021-03-16
Updated: 2021-03-16
Packaged: 2021-03-24 10:08:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,419
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30070653
Author URL: https://archiveofourown.org/users/DiaryOfMilo/pseuds/DiaryOfMilo
Summary: It's Milo's 18th birthday, and after celebrating, he's taken to the Baron's office to get initiated as a courtesan of The Baron's House.
Series: The Baron's House [1]
Series URL: https://archiveofourown.org/series/2212359
Comments: 1
Kudos: 7





	The First Night With The Baron

I can't say I wasn't nervous when I walked into the Baron's office that evening. He was sitting behind his large oak wood desk, relaxed, a mug of ale in his hand and a smile on his face. 

"Ah! There you are!" He said as he stood up and walked towards me, inviting me to sit on the red velvet couch that adorned a corner of his office. "Did you enjoy your birthday celebration? Turning eighteen is such an important moment in a man's life." 

"I did! Thank you, Sir." My cheeks felt warm, likely the effect of the mead I had earlier. The Baron had given the whole household the afternoon off to celebrate my birthday. He even ordered a lovely cake from the town's bakery, and allowed me half a cup of his own personal stock of mead. It was a lovely affair, and even some of the guards came by to play some music and sing. 

"Now, don't expect this to be a regular occurrence my boy, but, since this is a big milestone I wanted all of us to celebrate that. You've turned into such a lovely young man, the Mage truly outdid himself." The Baron placed his hand on my cheek, caressing me with his thumb. It was unexpected, but not unwelcome.

"The Mage? What do you mean Sir?" All my life, for as long as I could remember, the Mage had done nothing but make sure we were all healthy, especially the girls that worked for the Baron.

"He came up with a potion to… enhance a person's natural beauty you see. I ordered him to start treating you with it as soon as you started to change your voice. We had only used it on the girls before so we weren't really expecting such marvellous results. Softer skin and hair we were certain but not… everything else." He lowered his hand to my shoulder, slightly pulling down my tunic to reveal my collarbone and caress my neck. I shivered at the touch.

I always wondered why I was so different from all the men around me. Even though I worked just as hard, I could never seem to develop muscle like they did. My hips were rounder, and my thighs fuller. Even some of the girls would tease me saying they wished they had my hips. I didn't really mind, the men still treated me like an equal despite my more feminine physique, and it certainly didn't exclude me from doing heavy work around the house. 

I liked getting compliments for my hair, so I let it grow past my shoulders, almost to the middle of my back. I wore it braided most of the time so it wouldn't get in the way while I did my chores, otherwise I let it loose. Aiden, one of the guards, would always tell me my hair looked like the brightest, most beautiful pink blossoms, and would often place some small wildflowers on my hair. I thought it was cute, and if I placed an extra roll on his plate when I was on kitchen duty, no one was the wiser.

By far my biggest concern however, was my chest. The area around my nipples was slightly fuller than usual. I had seen the guards shirtless countless times and my chest looked nothing like theirs. I didn't mind most of the time, except on some days my nipples would be more sensitive and the slightest touch would send a jolt straight down my spine and a little moan would escape my lips. The difference was certainly rather obvious when I wore nothing but a tunic, so I started wearing a binder around my chest.

If the potion the Mage had created had a woman's beauty in mind, I was not surprised it had this kind of effect on me. "But, Sir, why would you order the Mage to do that? Why me?" 

"Part of it was… curiosity I'll admit, but once I started seeing the changes I _knew_ we had something special on our hands. You, my boy, are the first of many that will elevate what The Baron's House has to offer." He shifts and places both hands on my face, holding me softly to gaze into my eyes. "For eighteen years, you've been under my protection, but that changes tonight. I have yet to decide how soon I'll have you working with the girls. For now, I want you all to myself." 

He kissed me then. His beard tickled me but it felt… nice. I inhaled sharply, not expecting the rush of euphoria running through my body with just a simple touch of lips. He moved his hands down my arms and to my waist, and in one swift motion he had me sitting on his lap, my legs on each side of his, pulling me closer into a deeper kiss. I wrapped my arms around him and ran my hands through his short cropped hair. I moaned into his mouth when he pulled my tunic up and ran his hands over my thighs. 

This was nothing like my first kiss. I remembered it fondly, that warm spring morning when Aiden placed a wild violet in my hair, and his hand lingered a little longer than usual, and he gave me a quick kiss on the lips. It was a chaste kiss, and the fleeting moment of bliss I saw on his face was quickly replaced by panic as he repeated over and over "I shouldn't have done that" pacing up and down the courtyard. I calmed him down as best as I could, and I assured him that it would always remain our secret. Then I gave him my second kiss and left him there open mouthed. 

This was nothing like that. What the Baron was doing to me had my whole body in flames. He dug his hands into my buttocks like I'd seen countless men do to our girls, desperate to touch me everywhere he could reach. He lifted my tunic up and discarded it, taking a moment to gaze down my body. He pulled my binder down almost reverently, groaning at the sight of my uncovered chest. "Perfection" he said, and lowered himself to pepper soft kisses all over my chest. I whimpered and my nipples instantly hardened when his tongue swiped over them. I dug my nails on his shoulders as my cock twitched between my legs with every lick and soft bite. "I love how responsive your body is" the Baron groaned, pulling back to gaze at me again. "Get up and take off your underpants."

I did as the Baron asked, a little wobbly on my legs, but I managed to pull them down. I stood there naked in front of him while he undid his pants and pulled out his cock, stroking himself. "Turn around, legs slightly parted, and bend over." I faced the opposite wall, took a deep breath, and lowered my torso forward, exposing myself to the Baron. "Now I want you to reach back with your hands and spread your buttocks for me." 

As I held myself open for him, I could hear his groans getting louder. It was equal parts embarrassing and arousing doing this, just knowing how my body made the Baron feel dampened the shame, and it made _me_ feel good. It was making my cock leak so much, some drops fell on the floor right under me. "Please" I whispered. I wasn't sure what I was asking for, but I knew I wanted the Baron just as much as he wanted me. 

I heard him get up and walk slowly towards me. He pressed himself against my back, and I could feel his hot member poking at my back. It made me shiver and my knees buckled, but the Baron was quick to catch me. He led me to the room adjacent to his office, to his bedroom. It was my first time seeing it. No one was allowed in, not even for cleaning. A massive canopy bed was at the center, with another seating area in a corner. Massive wooden closets covered an entire wall, and there was a door I assumed led to his private bath. 

He lifted me and laid me down on his bed, then proceeded to remove his clothes. "Now, if the members of my house are to be trusted, and I do believe they are, you must still be a virgin," he looked at me expectantly, and I nodded, cheeks turning red as I confirmed that I was indeed still a virgin. He chuckled as he pulled down his pants. "I ought to give the entire household a raise for being able to resist such a big temptation" he grabbed me by the legs and pulled me down to the edge of the bed, spreading my legs and caressing the inside of my thighs. "Tell me boy, do you know what men do when they are together like this?"

"Yes, Sir" I replied with a trembling voice. He came closer then, his cock lining up with mine, rubbing against each other. Mine was considerably smaller compared to his, but the groans of pleasure coming out of the Baron let me know that it was exactly what he preferred. He pulled me into a tight embrace, and my legs instinctively wrapped around him, holding him close to me. He bit into my neck as he kept grinding our cocks together, almost growling. 

"I can't hold on anymore, I _need_ to have you," he said, I could hear the want in his voice, so I pulled him down for another kiss, I didn't think at this point I could form a coherent sentence so I just put all my desperation into the kiss, to let him know that I wanted this just as much. The Baron pulled back just long enough to grab something from his nightstand and we settled in the middle of his bed, me still on my back with my legs spread for him. He opened the small bottle he'd grabbed, and poured some sweet smelling oil over his fingers. "We need to do this so I don't hurt you, alright?" He said as he guided his hand between my legs and spread the oil over my most secret place. 

I gasped as he pushed one finger inside me, adding more oil and working it in along with his finger. Even knowing what was coming, it felt strange to be touched like this, yet my cock was still as hard as it had been all night. When the Baron pushed a second finger in, I could not stop the moan that left my lips. He pressed them more insistently, pushing them in and out of me with such force my whole body moved. "More" I begged him, looking up at him. 

He pulled his fingers out and positioned himself between my legs, his cock pressed against my entrance. "Ready?" He asked me, and I nodded. He smiled at me and started pressing against my hole, the head of his cock slowly breaching past my resistance until it gave in, letting him in. I winced at the intrusion, his cock being considerably longer and thicker than his fingers. 

"That's it boy, just relax and let me in," he kept pressing, and I could feel every inch of his cock stretching me open. When he bottomed out I let out a breathy sigh of relief. "You're loving this, aren't you Milo? Your hole was made to take cock boy, squeezing me tightly like this," he pulled back slightly and thrusted into me, coaxing a moan out of me. "You're gonna have lots of clients lining up for a chance at you."

He pulled back further, almost all the way out before sinking back in slowly. I gasped when his cock pressed a spot inside me that made me jolt in pleasure. He picked up the pace, pressing against my spot over and over until I was a moaning writhing mess under him. He kept running his thumbs over my nipples as he fucked me. The over stimulation was making my cock leak like crazy, forming a pool of precum in my belly.

The Baron dripped more oil into my hole, easing his thrusts so he could fuck me harder, the bed creaking under the force, the slaps of skin against skin reverberating around the room. I was sure the whole house could hear me moaning, yet I didn't care. I reached for him, running my hands over his pecs and down his abs, marveling at his muscular body. "Sir, please, I'm close" I whimpered, feeling my orgasm building, which made me tighten around the Baron's cock.

"Come for me boy, show me how much you love having cock up your ass" he changed his pace to short hard thrusts that expertly targeted my spot. My back arched up off the bed as spurt after spurt of cum erupted from my cock, spraying all over my belly and even up to my chest. The Baron followed me shortly after, slamming into me one last time and staying deep inside me while he filled me with his hot seed. He leaned down to kiss me, slowly thrusting into me and swallowing my moans as he pressed my hyper sensitive cock between us.

He rolled us over, his cock popping out of me with a wet sound. He pulled me on top of him, one of his hands reaching behind me to tease my sloppy stretched out hole, fingering his cum back into me. "You were perfect Milo, you'll be a great addition to The Baron's House. We'll start your training next week. The girls will teach you much more than I ever could," he chuckled. "You'll sleep in my bed tonight, but after that you'll be assigned your own room. You're allowed to decorate it however you want, within limits of course, and we'll get you some new outfits for your debut. A servant's tunic will no longer do my boy. And no more binders, no need to hide such pretty things anymore."

It made me nervous and excited at the same time, knowing I'd become 'one of the girls', but I was eager to prove my worth to the Baron. "Thank you," I said, "for giving me a chance. I won't let you down Sir."

"I know you won't Milo. I know you won't."

**Author's Note:**

> Hello reader! This is the first of what I hope will be a series of short stories about Milo and his time as a courtesan of The Baron's House. I hope you enjoyed it!


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